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Clothing has always been important to me, and while I’ve never been a particularly trendy dresser, I’ve always cared about what I wear and how I present myself.

As a high school student I developed an eccentric sense of style that culled from Army Navy stores, flea markets, thrift stores, and my grandmother, which earned me the dubious title of “best dressed” from my choir. (Long live art kids.) Fast forward almost ten years and I still have a penchant for ripped tights, messy hair, weird fitting cardigans, and massive scarves, so dressing appropriately for work is a continuous challenge for me, even in a casual environment like Safari.

Below, some things I’ve learned:

1. Choose a color palette and develop a uniform

I chose black as my color palette because black is versatile, dynamic, and simple. While black clothing can be difficult to match together, (never assume that two black pieces are going to match!) they are also easy to accessorize, look more polished, wash better, and generally wrinkle less than light colored clothing. Also, if you are like me, all your white dresses will have coffee stains, which are fortunately easily covered with large scarves. (Just kidding!)

NYMag ran a series of excellent posts on stylish women and uniforms, and I largely echo those sentiments. Wearing a uniform has made getting dressed in the morning easier and infinitely more chic.

2. Purge often

I had bedbugs in college, which meant I had to get rid of a fairly large collection of hideous patterned 1980s sweaters collected from years of thrifting.

At the time I was devastated, but now I see that experience as a blessing because it taught me the importance of purging my clothes often. Are your favorite pair of pants pilled beyond recognition? Do you have dresses that look wrinkled no matter how many times you iron them? What’s sitting in the back of your drawer that you never wear? Give these clothes to charity, sell them to a consignment shop, or have a clothes swap with your friends: there’s no reason to hold onto things you don’t wear, and getting rid of clothing means you have more room for the things you actually feel good in.

3. Accessorize

Accessories are an easy way to make every outfit feel more complete, from scarves to statement necklaces to big vintage rings. I inherited a large collection of scarves from my grandmothers, and I scour vintage stores, flea markets, and consignment sales for costume jewelry. I also try to buy simple, inexpensive pieces from local designers at small boutiques in the area.

I rarely leave the house without jewelry and a subtle perfume. A distinctive scent can help you feel more polished. (I wear Jo Malone 154.) If you’re scent sensitive, I highly recommend finding an organic essential oil you enjoy. A few drops can make the whole day brighter.

jennie-in-dress

Working it at work

4. Quality always trumps quantity

While we live in an age of fast fashion, you can find well-made clothes for less if you take some time to think about your buying values. While I occasionally buy for convenience, I also am extremely aware of the quality of my clothes due to years of trawling consignment stores for top designers like Marc Jacobs and Chloe.

Good quality clothing doesn’t have to be expensive.. Brass, a local Boston startup that works directly with factories to provide high quality garments for less, ran a piece last year about how to judge quality in clothing, and I’ve found it helpful when shopping for work clothes.

5. Never buy retail

Like one of my fashion role models, Fran Fine, I would never buy retail. (Particularly if my “cousin” was Todd Oldham!)

For better or worse, most retailers exist in a constant sales model where it’s easy to patiently wait for a piece to go slightly out of season in order to get a deal. My focus on sales has helped me find some amazing pieces from high-end designers for much less than their original price. 

6. Don’t forget your shoes

I am from a “shoe family” (I’m the first in three generations not to work in the women’s shoe business!) so shoes are clearly important to me. With shoes, price does reflect quality and comfort, so it’s worth investing in a few good pairs that you can wear for a long time.

Also, meet your local cobbler and make friends! If you love a pair of shoes and wear them out they can usually be fixed.

Ethical shopping for the fashion-conscious

Before I buy, I try to think about the ethical and environmental consequences of buying an article of clothing, which is why you’re more likely to find me at a local boutique or consignment store than a mall. I also have a strong belief in “less is more.” I buy clothes infrequently, though I often wander boutiques and stores or browse sites for fashion ideas that I can incorporate into my wardrobe.

Local consignment stores

Depending on your neighborhood and geographic area, consignment can be a lifesaver. (Pro tip: the Beacon Hill Second Time Around is the best consignment in the Boston area!) Consigning is usually easier if you wear a very common or very small size and are willing to spend a good deal of time sifting through ill-fitting, pilled, or otherwise weird clothing to find something special, but I know lots of women of every size who love consignment stores.

If you are looking for work clothes, I wouldn’t bother with places like Goodwill unless you have a lot of time and patience to sort through clothing. (That girl you met at a party wearing an Alexander Wang from Goodwill was probably lying.)

Boutiques and local designers

Most of my favorite clothes and accessories come from local boutiques and traveling. Boutiques tend to be more expensive, but in addition to supporting local business, I find my most unique pieces through boutique shopping. In Boston, my favorite boutiques include Oona’s, Tess (when I can afford it!), Mint Julep, Holiday, and December Thieves and Magpie for accessories. Go at the end of the season to find the best deals.

I find that it’s usually it’s worth splurging for local design as well. In San Francisco, I discovered the designer Curator, and in Portland I discovered the incredible textile designer Sara Bergman. These pieces have stayed with me because they’re unique, special, and remind me of my time traveling.

Everlane and Brass

A friend of mine describes Everlane as “Eileen Fisher for 20-somethings,” and their casual, inexpensive, comfortable clothes are my absolute favorites, though they still have a slightly limited selection. Brass currently sells only dresses and I have yet to get off the waitlist, but I think their online store is gorgeous. I like these more “ethical” producers, who work directly with factories to ensure fair treatment for workers, and have been pleased with the quality of their clothing.

My favorite fashionable places on the Internet for inspiration:

  • The Cut (the best blog I read and my procrastination tool to the max. Want to see every outfit Michelle Obama ever wore? Here’s your chance.)
  • Cheap Chic (this article tells you everything you need to know. Required reading for fashionable people.)
  • Goop (easily mocked, for sure, but it really is great for recipes, yoga poses, and very expensive clothing I can never afford. A girl can dream, right?)
  • Refinery29 and PopSugar (sort through the clickbait for great advice)
  • Dazed Digital (for your high-fashion techno soul)
  • Tavi Gevinson’s Instagram feed (I’ve been discovering designers through Tavi since she was 12 and I was 22)
  • Man Repeller (a bit chatty and light, but Leandra knows everything about the fashion world)

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